2,2-disubstituierte cyclopentan-1,3-dione—2

Schick, H.; Schwarz, H.; Finger, Angelika; Schwarz, S.

doi:10.1016/0040-4020(82)85114-4

Cited by 33 publications

(5 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, the present prenylation could be related to the reported C ‐mono‐ and gem ‐dicrotylation of 1,3‐cyclohexanedione in the presence of potassium hydroxide in water 21. Schick and co‐workers have shown that the O / C ratio for the alkylation of 2‐methyl‐1,3‐cyclopentanedione was minimized when using a reactive halide, such as allyl bromide, and water as the solvent 22. The results reported here are consistent with these different observations and proposals.…”

Section: Resultsmentioning

confidence: 68%

Synthesis of Polyprenylated Benzoylphloroglucinols by Regioselective Prenylation of Phloroglucinol in an Aqueous Medium

Raikar¹,

Nuhant²,

Delpech³

et al. 2008

Eur J Org Chem

View full text Add to dashboard Cite

Regioselective tri‐C‐prenylation of phloroglucinol, leading to a compound with gem‐disubstitution, has been achieved with prenyl bromide in the presence of potassium hydroxide in an aqueous medium. Geranyl‐ and isolavandulylphloroglucinol, obtained by ortho‐lithiation, were diprenylated under the same conditions. C‐Benzoylation of the trialkylated derivatives using benzoyl cyanide in the presence of triethylamine afforded two natural products, grandone and kolanone, and an isomer of weddellianone A. Attemped electrophilic cyclization reactions, aimed at a biomimetic synthesis of polycyclic polyprenylated acylphloroglucinols (PPAPs), are also reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

show abstract

Section: Resultsmentioning

confidence: 68%

Synthesis of Polyprenylated Benzoylphloroglucinols by Regioselective Prenylation of Phloroglucinol in an Aqueous Medium

Raikar¹,

Nuhant²,

Delpech³

et al. 2008

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…The use of DMF resulted in the highest level of the bisalkylated impurity, and dichloromethane did not offer any improvement (Table , entries 11 and 12). Among the solvents investigated, toluene provided the best in-process impurity profile of keto ester 21 …”

Section: Resultsmentioning

confidence: 99%

Development of a Practical Synthesis of a Functionalized Pyrrolo[2,1-f][1,2,4]triazine Nucleus

Zheng

Conlon

Corbett

et al. 2012

Org. Process Res. Dev.

View full text Add to dashboard Cite

Functionalized pyrrolotriazine 1b is a key heterocyclic building block in the synthesis of BMS-690514, a potent anticancer agent. Described herein are our development activities that led to the efficient preparation of 1b on a large scale. The key transformations include a selective C-alkylation of an oxalacetate salt with a hydrazonyl bromide to form a 2-hydrazonoethyl-3-oxosuccinate, followed by cyclodehydration to an aminopyrrole. Subsequent deprotection and condensation with formamidine afforded the pyrrolotriazine scaffold. Further elaboration of this core provided the desired pyrrolotriazinyl amine.

show abstract

“…However, C-alkylations of these species can be conducted reasonably successfully in protic solvents, e.g. water 280. Trost and Curran 281 have reported high yields for the C-alkylation of cyclic 1,3-diketones with allylic acetates in the presence of palladium(O) catalysts and DBU (Scheme 80).…”

mentioning

confidence: 99%